He Turned Down JPMorgan to Build a Luxury Airbnb Empire

Today we’re sitting down with Rajan Chida - an entrepreneur who turned down a job offer at JPMorgan to build his own path. Instead of taking the traditional 9-5 route, Rajan co-founded Royal Oak Retreat, a luxury cabin experience in Virginia, where he’s building more than just a business he’s building a lifestyle.

We dive into what it’s like going against cultural expectations, buying land, building a retreat from scratch, and why betting on yourself can be the most rewarding risk you ever take.

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Royal Oak Retreat: https://www.royaloakretreat.com

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Time codes

0:00 - WELCOME TO HALF PAST CHAI

2:27 - Who is Rajan Chida?

8:51 - Where did the money come from?

11:53 - How did the shoe business start?

16:30 - How Rajan met his business partner, Renzo

22:16 - How did the shoe business help you with what you’re doing now

25:50 - The long game.

34:14 - Do you ever question what you’re doing?

37:05 - What happened when you went viral?

40:01 - EVERYTHING ON YOUR PHONE

46:40 - Advice for someone trying to start their own business

50:08 - The technical side of the business

55:13 - Rapid Fire